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1,2-Dichloroethane → HCID 21837214, compound

HRID 1740597
Notes
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Reaction equation

HRID 1740597 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[F:15][C:16]([F:30])([F:29])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26](O)=[O:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:15][C:16]([F:29])([F:30])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1)=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 13461-(2-Methoxyphenyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18700172HCID 18700172, compound

Product 1

HCID 21837214HCID 21837214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-methoxyphenylpiperazine (0.062 g, 0.32 mmol) and 2-(2,2,2-trifluoroethoxy)phenylacetic acid (0.075 mg, 0.32 mmol) in DMF (1 mL) was added EDC (0.115 g, 0.40 mmol), HOBT (0.049 g, 0.32 mmol), and DIEA (0.055 mL, 0.32 mmol). The mixture was stirred at ambient temperature for 18 h. The DMF was removed under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The EtOAc layer was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by preparative TLC using 1:1 EtOAc:hexane as eluant. The title compound was obtained as an amorphous solid.

Workup

  1. customThe DMF was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. dry with materialThe EtOAc layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-da77aa0e397c437e9457fd9f913790a5
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05968938

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes